


A Hell of a Time

by Mishapocalyptic



Series: Leonardo DiCaprio: Hunter In Training [1]
Category: Supernatural
Genre: Alternate Universe - Canon, Crack Crossover, I can't explain this, M/M
Language: English
Status: Completed
Published: 2014-02-03
Updated: 2014-02-03
Packaged: 2018-01-11 01:52:14
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,732
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1167201
Author URL: https://archiveofourown.org/users/Mishapocalyptic/pseuds/Mishapocalyptic
Summary: <blockquote class="userstuff">
              <p>Leo DiCaprio finally gets his Oscar, but it turns out that he’s made a cross-roads deal. He only has until the end of his acceptance speech to live. Sam and Dean must figure out how to break his deal.</p>
            </blockquote>





	A Hell of a Time

_Industry, CA, 2004. About 20 miles outside of Los Angeles._

The young man around 30 years old stood at a crossroads. He looked at the box in his hands, filled with strange things that took him forever to find. He bent over, digging a shallow hole in the ground with his hands, and then putting the box in the hole. He covered it back up with the dirt he’d dug out. There was a gust of wind, and he stood up. He heard a sweet laughing and turned around.

“Leonardo DiCaprio?” a woman chuckled. “I never thought I’d see you here.”

“Who are you?” he asked her. She was beautiful, with long, dark hair cascading in perfect curls around her shoulders. Her face was pale, almost lacking blood pulse. She smiled, flashing a brilliantly white set of teeth, and she blinked. Her eyes became red, and after blinking again, they were back to the shade of chocolatey brown they had been before.

“Honey,” she cooed. “What did you think you were doing with that box? Did you think nothing would happen? That this was just an urban myth?” Leonardo’s breath was gone. He couldn’t form words. He didn’t know what he was expecting anyway. “Leo...” She clicked her tongue. “I can call you Leo, right?” He nodded meekly. “So, Leo, what do you want?” Her tone became seductive, and he suddenly felt as though he trusted her even though he knew he shouldn’t have.

“I-I... I want to win an Oscar,” Leo stuttered. “Well, specifically, I want to have really good movies and win at least one Oscar for one of them.” She smiled viciously. “Can you do that?”

“Oh, of course, dear.” She stepped forward, intruding on his personal space.

“So... Uh... Do we shake on it?” Leonardo’s breath hitched as she stepped up flush with him.

“Not quite...” She smirked, and then grabbed his neck and pulled him down, locking her lips with his. She pulled away. “The deal is done. You’ll have your Oscar.”  
“Can you tell me when?” he asked her eagerly.

“No. That’ll be a surprise.” He blinked and then she was gone. He heard a car engine from behind him and turned toward it. A figure rushed out of the driver side door after cutting the engine.

“Don’t tell me you made the deal,” the man shouted. Leo didn’t say anything. “Dammit, Leo! I told you not to!”

“I’m sorry, Dean... But once she got here, I-I couldn’t help it. She made me want to make the deal!” Dean Winchester sighed angrily.

“Alright. Here’s what gonna happen: in about 10 years, call me when you start seeing hallucinations of big, black dogs. I can’t do anything for you right now, but maybe by then I’ll be able to help you.” Leo nodded.

“Just... Don’t leave me when the time comes. If you can help me in anyway, I’d be eternally grateful.”

“Yeah, whatever.” Dean sulked back to his car. “Let’s get you back into town. The Oscars are tomorrow.” Leo ambled into the passenger seat of Dean’s car and they drove back into Los Angeles.

Dean dropped him off on a street corner about 2 blocks from where Leo told him to. As Dean drove away, he secretly hoped he wouldn’t hear from Leonardo DiCaprio ever again.

 

_Lebanon, Kansas, 2014._

A ’67 Chevy Impala drove down the highway. Dean and Sam Winchester rode in the front seat, their former-angel Castiel sitting in the back. They were driving back to their bunker, a former Men of Letters headquarters. As they pulled around the hill to the bunker, Dean’s phone began to ring.

“Will you grab that for me?” Dean asked his brother.

“Sure, Dean. Of course I can pick up your phone for you,” Sam sassed. Nonetheless, he picked up the phone. “Hello?”

“Dean Winchester?” a strikingly familiar voice asked.

“Uh, no. This is his brother, Sam.” Dean cut off the car.

“Well, can I talk to him?” It suddenly struck Sam who it was. He got out of the car.

“Yeah. Just a second.” Sam covered the receiver. “Dean!” he whisper-shouted. “Why is Leonardo DiCaprio calling you?”

“It’s Leonardo DiCaprio?! Give me the phone!” Castiel scrunched his eyebrows together.

“Who is Leonardo DiCaprio?” Cas asked.

“He’s a movie star,” Sam answered.

“Why is he calling Dean?”

“No idea.” Dean snatched the phone from his brother.

“Leo!” he greeted. “Is it time?”

“Yeah...” Leo answered, sounding depressed.

“Well, you’re in luck. We know how to kill hell hounds.”

“Great! There’s a complication...”

“What?” Dean became concerned. 

“The Oscars are on the same day as my last day...”

“Damn.” Dean cast a glance at Sam and Castiel.

“Just come out here. I’ll send a plane. Where should I pick you guys up at?”

“I think we’ll drive,” Dean stated nervously. “I have a thing about planes.”

“Can you get here in time?” Dean laughed.

“With my driving, yes. Plus, there’s three of us. We can swap out. We’ll be fine.”

“Okay. Just get here. I have to be composed for the Oscars. I think I’m finally getting my Oscar.”

“This is a crap deal. You get your Oscar the night they take your soul back.”

“Yeah, I know...” Leo sighed. “Just call me when you get to town. I have things to explain to you.”

“Can do.” Dean hung up and turned to the others. “Well, Leo made a demon deal 10 years back. I was with him, because a friend of his had just been dragged down into Hell and he got caught in the middle of it. I tried to stop him, but I was too late. I told him to call when the time came and I’d see if I could help him.” Sam nodded slowly, and Cas seemed just as confused as ever. Dean went inside to switch out his clothes. When he came back, Sam and Cas were ready to go.

The three drove to L.A. It only took a day and a half. Dean called Leonardo as they walked into a hotel room. They set up a meeting place, namely, Leo’s house. When they arrived, Leo was freaking out. Dean and Sam could hardly believe Leo’s house; it was nicer than “Jared Padalecki’s” house when they got thrown into an alternate universe.

“I can get two of you in, but you’ll have to go as a pair,” Leo said when discussing tactics. 

“A pair..?” Dean asked. 

“Like a couple...?” Sam echoed. The two looked at each other.

“Well...” Leo started. “Yes.” Sam laughed.

“Looks like Dean and Cas’ll be going with you!” Sam exclaimed. He secretly thought that Cas and Dean were interested in each other, but he’d never say anything because Dean’d blow a gasket. Dean looked over at Sam and glared before resigning himself to the reality.

“Yeah, I guess we will... Cas, you up for that?” Dean looked over at him. Castiel seemed very confused.

“Sam, we’ll get you in somehow,” Leo reassured. Sam nodded.

“I’m not too concerned,” Sam responded.

“Sam, do you still have those glasses we used during the trials?” Dean asked. Sam nodded. “Good, we’ll need those. Do you think we can get another pair for Cas?”

“I don’t think so.”

“I do not need them,” Cas said.

“Why?”

“If you have the glasses, then you can tell me where it is. I do happen to have a keen sense of smell.” 

“Right. Sorry.” Dean turned to Leo after answering awkwardly. “Do you know of a way that we can get tuxes? We’re broke here, so...”

“Of course,” Leo smiled jovially. “Castiel, I think you’ll fit in one of mine, but Dean, we’ll have to get you and Sam fitted.”

“Leo... I don’t think Cas is short enough to fit in your tux,” Dean joked.

“I’m 6 feet tall!” Leo shouted indignantly. Dean snickered.

“I know, dude. Calm down.” Cas was very confused by all of this.

“I don’t understand. What are we fitting?” Cas asked, tilting his head innocently.

“Tuxes. And if you two,” Leo motioned at Sam and Dean while he said this, “Want to come back in, say, an hour, I can get you fixed up. You’ll have them by tomorrow morning.” Dean and Sam agreed, both thinking it was an excellent plan. Before they left, they placed Devil’s Shoestring around the doors and windows, telling Leo that he mustn’t move it. It would keep the hell hounds at bay.

When Sam, Dean, and Castiel came back after a rushed lunch, a stuffy man was waiting in the parlor that Leonardo lead them to. He turned his nose up as Leo pushed Sam and Dean forward.

“Plaid? That is so last season,” he scoffed, eyeing the two brother’s apparel.

“Um,” Leo started. “This is Jacques. He’s my personal tailor. He’ll get you fitted.” He turned to Cas. “Come with me.” He motioned as he left the parlor. “We’ll make sure one of my tuxes fits you. I’ll let you wear the white one. You’ll contrast with Dean and it’ll make you seem more like a red carpet couple.” Dean grimaced and Cas blanched. However, Cas followed obediently.

“Alright, heathens,” Jacques said. “I’ll start with the moose.” He pointed at Sam and indicated that he should move. Sam looked over at Dean as he walked onto a platform set up in the middle of the room. “Now, stand still. If I lift your arm, let me lift it. Don’t for any reason move your muscles on your own.” Sam scrunched his eyebrows together in confusion. Jacques took his height first, and then measured from his hips to his feet. Then, from shoulder to the top of his bum, the width of his shoulders, the length of his arms. Sam felt slightly violated, and Dean snickered at his brother’s discomfort.

Dean wasn’t laughing for too long, though, because soon he understood. Jacques went through the whole shebang with him, too. The brothers were surprised with how fast that was. They walked out of the parlor after Jacques had dismissed them, only to find Leo and Cas laughing in the sitting room. The two men had glasses of liquor, and a fancy bottle of gin sat on the table in between their chairs, two empty glasses next to it.

“Took you two long enough,” Leo chuckled. “Cas here fits perfectly in my tux.” Cas grinned and raised his glass in a Gatsby-esque manner. He smiled, a true genuine smile, and for some reason, Dean found himself liking this plan. “Sit, boys, have a drink. We need to go over the basic plan and Cas and Dean need to learn some basic etiquette.” Sam and Dean sat down, Sam in a chair next to Leo, and Dean on the love seat next to Cas.

As the four sipped their gin, they went over how they’d get Sam in, and how Dean and Cas should act. Dean found himself resisting the urge to put his arm on the back of the couch, afraid that Cas would take it the wrong way. He also wondered why he thought Cas would take it the wrong way.

“Dean, you realise that you and Cas have to act like a gay couple, right?” Leo asked. “That means holding hands, arms on waists, maybe a kiss or two on the cheek. Are you sure you’re okay with that? Otherwise we can try to get you in another way.”  
“No no. It’s the easiest way to do this,” Dean assured him.

“Okay, then. Come by in the morning for your tuxes, and then I’ll call you when we’re on our way. We’ll be riding in different limos, but we can come get you.” Team Free Will, as they called themselves, nodded. They stood up and thanked Leo and assured him that he’d probably be fine before leaving. As Leonardo shut the door behind them, he let out a shaky breath. He checked all of the Devil’s Shoestring before settling in for the night, locking every window and door.

Dean and Sam came the next morning to pick up the tuxedos. Cas’s had been sent home with them the night before. They mulled around until after lunch, when they figured they should get ready. Sam slicked his hair back with his tux. Dean left his hair as is. Dean had to help Castiel with his tux, considering Cas didn’t actually know how to put a tux on. The cummerbund and bow tie were the bane of his existence in that moment. Dean mussed up Cas’s hair for him, saying that if they were gonna be a couple for the night, his boyfriend had to have sexy hair.

Dean relished that coming out of his mouth. Boyfriend. He liked the ring of that, as long as Cas was the boyfriend. He was pulled out of his reverie when they heard a knock on the door. Sam grabbed his gun and tucked it into the back of his pants. Dean unhappily didn’t grab a gun, knowing he’d never get in with one on his person. Sam cautiously peeked out of the peep hole, then relaxed.

“It’s just Leonardo.” He opened the door, and Leo grinned at them. Dean could see that he had fixed some Devil’s Shoestring to his lapel. Leo lead them to the cars, and motioned that Dean and Cas were in the one behind his, and Sam could ride wherever he wanted because he was getting out around back.

Dean fidgeted in the car. Cas could tell, and placed a hand on his knee.

“Calm down,” he insisted. “Is it this whole couple business?” Dean nodded. “Look, just remember that it doesn’t mean anything. It’s just a job.” Dean nodded again, heart breaking ever so slightly. Cas, too, felt a pain at what he had said. But he had thought it for the best.

When they arrived, the limos pulled up. Leo stepped out first with his date (some girl he’d met a few weeks prior), and then his car pulled away with Sam inside. Dean and Cas’ car pulled up, and suddenly someone was opening their door, lights flashing as people took pictures, reporters asking who they were. Dean remembered the part he had to play, and grabbed Cas’s hand as they got out. Leo came over and clapped him on the shoulder, smiling and telling the reporters that Dean and Cas were childhood friends. He explained that he wanted them there for his big day.

Dean and Cas played along, making up answers along the lines of what Leo had told them. They laughed, and held hands, and Dean constantly kept his arm around Cas’s waist. At one point, they were asked how long they had been together. Dean looked lovingly at Cas, and said,

“Oh, about 5 years. Cas here saved my life.” Dean looked down and before he realised it, Cas had leaned up and kissed him. Dean’s eyes fluttered closed and then the kiss was over. Dean smiled at him and Cas smiled back. Some of the girls in the onlooking crowd giggled.

“But, Dean,” on reporter insisted. “It is Dean right?” He nodded. “You’re so good looking; you could have had any girl you wanted. Why him?”

“Cas and I have always had a profound bond,” Dean started. Cas patted his arm, right on the hand print left on Dean 6 years earlier. “So when he came to my rescue, it all clicked and I knew I wanted to be with him.” Castiel just smiled, and then looked over at Leo over Dean’s shoulder.

“Dean, we need to move on,” Cas said sweetly. Dean nodded, and the pair said goodbye to the reporters. They ambled up to Leo, who leaned over to them.

“We’re going in now. That was pretty convincing.” He raised his eyebrows appreciatively. Cas and Dean just smiled. “They’re gonna show us to our seats, and then I’m going to suggest you use the bathroom before the show starts.” They nodded. The four of them (not forgetting Leo’s date) walked inside and were directed towards seats near the front.

After sitting down, Cas and Dean excused themselves to the bathroom. Leo’s date winked at them, but this was actually part of the plan. The two looked around, making sure the coast was clear, and after making sure the bathroom was clear, they unlocked the window at the top of the wall.

“Finally,” Sam huffed as he clambered down, his long limbs proving to be an obstacle he hadn’t accounted for.

“Hey, at least we were able to,” Dean retorted. Sam straightened up and fixed his shirt. Then, he opened the door a crack and peered out before slinking away to the backstage area. Cas and Dean waited a few minutes so it wouldn’t look suspicious, and while they waited, Dean realised something. “Cas?”

“Yes, Dean?” Castiel looked up at him, and without thinking, Dean leaned down and kissed Cas. It was short, but it said everything he was feeling. “Um... There’s no one here..?” Cas blushed and smiled a bit.

“I know,” Dean smirked. He extended a hand toward Cas, and the former angel took it without hesitation. They walked out and quickly returned to their seats. Leo cocked an eyebrow but didn’t say anything.

As it neared the end of the program, Leonardo made a motion toward the two hunters that it was time. Dean and Cas followed him backstage and met up with Sam.

“Are we ready?” Sam asked.

“I’m still unsure of my role in this plan,” Cas stated.

“Make sure Leo is okay. Set up the Devil’s Shoestring around the wings, and stay inside of it,” Dean instructed.

“I am quite capable of helping, Dean.”

“I know, but I want you to be safe. Plus, we only have two pairs of glasses.” Dean moved closer. “Please, just be safe. I’ve lost you too many times.”

“Dean,” Sam called. “I’m glad you’ve admitted it to yourself, but we’ve gotta cut this chick moment short. We’ve got 15 minutes.” Dean nodded, still looking at Cas. He stepped back, and Cas smiled.

“It’ll be okay, Dean. I’ll be fine,” Cas reassured. He steered Leo away to the wings and set about putting down Devil’s Shoestring.

 

***** ***** ***** 

 

Dean heard it first. It was a low growl and gave Dean flashbacks to when he was in the 11th hour himself. He nodded to Sam and they slipped the glasses on. Almost instantaneously, they saw a shadowy figure prowling around them.

“Hey boy,” Dean chided. “I’d hate to send you home without dinner... Oh wait, I don’t.” Dean smirked and lunged forward, angel blade in hand. He grabbed around the hell hound’s neck and swung his leg over its back, holding on for dear life. “Sam! Get him!”

“On it!” Sam slid underneath the hell hound while it was occupied with getting Dean off its back. He tried to stab its chest, but it was thrashing around so much that he was in danger of stabbing Dean’s leg. “Dean, keep it still! I can’t get it!”

“Dammit, Sam!” Dean threw all of his weight to the side, throwing the hell hound off balance and pulling the two of them onto the floor. The hound rolled on top of him, and Sam scrambled over, stabbing it through the chest and pushing it off of Dean. “Thanks.” Sam helped Dean up, and both breathed a sigh of relief.

“Think that’s it?”

“I think so.” Alas, the brothers spoke too soon.

“Hello, boys,” a smooth voice said from behind them. They turned.

“Really, Crowley? A personal appearance?” Dean asked incredulously.

“You killed my pet. Plus, I believe Mr. DiCaprio owes me a soul.”

“Crowley, do you really want it?” Sam asked. “Just let him off the hook. We all know he was gonna get an Oscar without your help.”

“I’m afraid that’s not how it works. If you’ll excuse me.” Crowley tried to pass but got thrown back. He looked up and saw a devil trap drawn discreetly on the ceiling. “I see I was expected.”

“Of course. We’ll let you our if you let Leo out of his deal,” Dean proposed.

“And why would I do that?” Crowley countered.

“Because we won’t interfere with deals anymore,” Sam promised.

“How can I believe that?”

“We’ll sign a contract if we have to,” Dean answered gruffly.

“Alright, Squirrel. I’ll believe you this time. But if you braked this promise, Leo’s soul is the first to go.” Crowley smiled evilly.

“Deal.” Dean stuck his hand out for Crowley to shake, and Crowley shook his head.

“You know how it works, Dean.” Crowley clicked his tongue, and Dean grimaced in disgust.

“I’m not sure that I can do that...” Sam huffed at Dean’s response.

“Fine. I’ll do it.” Sam stepped forward and before Dean could protest, Sam quickly kissed Crowley.

“You’re not as fun as Bobby,” Crowley purred. “But, since both of you are doing it, Dean still has to kiss me. I like your enthusiasm, though, Moose.” Dean groaned and followed Sam’s exampled, wiping his mouth on his sleeve immediately afterward. “Will you let me out now?”

“Alright,” Sam said. He grabbed a chair and stood up on it, scratching a part of the trap with Ruby’s knife.

“Toodles,” Crowley sand. He snapped his fingers and was gone. Sam glanced at his watch. 12:02 am. They’d won. Cas came running in, and Leo strolled along behind him. Cas tackled Dean in a hug.

“You’re okay? No trouble?” Cas asked quickly.

“I’m fine. Really. It was nothing we couldn’t handle.” Dean smiled at Cas, and Cas smiled back.

“So I’m good to go?” Leo asked carefully.

“Yeah. You’re free,” Sam said.

“Thank you guys. I can’t ever repay you enough.” Leo smiled genuinely. “If you ever need anything, just call me. Now, you guys might wanna run out the back after tearing up the backstage.” The trio nodded and waved goodbye.

The cool of night greeted them, and Dean took Cas’s hand in his own. All three breathed a sigh of relief.

“Not too bad,” Sam said. “Could’ve been a cleaner job, but we got it done.” Dean and Cas nodded.

“Let’s head out. We’re already too conspicuous,” Dean stated. Sam and Cas agreed, and they all headed back to the hotel and the Impala to go back to the bunker.

**Author's Note:**

> I don't... I don't know how to explain this. I know this prompt has been circling tumblr, but I didn't see that until after I had written this...


End file.
